I've been working on Premium Poker Tools for over two years now. I'm at a point where things aren't looking so hot, and I need to sit down and do some hard thinking. What better way to do that then to write on LessWrong!


To understand my journey with Premium Poker Tools, I think you have to first understand a little bit about me and what I'm doing with my life. In short, I want to start startups, make a lot of money, and use the money to a) be financially independent, and b) do good for the world.

I spent about two years in college working on a startup that went nowhere. After that, I managed to get an entry level job as a web developer. I was a pretty bad at the time. I spent about 11 months at that job before getting fired. I quickly got another job, but got fired 5 months into that one. In both cases, it was a mix of a) me clearly not being a "company guy", and instead wanting to be done at 5pm so I could go off and do what's best for me, b) clashes with authority figures, and c) being a slow programmer.

After the second job, I moved to Vegas to be with my now girlfriend. I had about $85,000 saved up in the bank, and my plan was the following: 1) get better at programming, 2) freelance a little and save up some more money, 3) start a startup. And then from there repeat steps 2 and 3 (and maybe 1) until I succeed with a startup. After that, the plan would be some mix of 1) figuring out how to use the money for good, 2) starting or investing in more startups, and 3) enjoying myself.

Self-studying computer science

I spent my first year in Vegas self-studying computer science. It was alright. Idk. I feel like I should have came away from that year making a lot more progress than I did, but at the same time, I did learn a lot.

In general, I've always planned on living the digital nomad life. At least until I find a place I like enough to want to settle down in. But I'm pretty sure that'll take some time, and that I'll end up spending time in a lot of different places. Anyway, I find myself living in Vegas. Poker is a thing in Vegas. I figure that I should spend some time on hobbies, and poker seems cool, so I feel like I should give poker a shot while I happen to be in Vegas. I won't have another opportunity like this. Or so my thought process was at the time.

So, during that first year, I spend some of my time learning and playing poker. I have a lot to say about poker. I think it's a great game for rationalists and people into challenging themselves and self-improvement. I'll have to write about that in another post some time.

As I learn about poker, I see these two apps come up over and over again: Flopzilla and Equilab. They're in books, and videos, and blog posts. People talk about them in poker forums. It seems like if you play poker, you really need to have these apps. They let you run simulations and see things like how often A3s beats JJ, and how often 76s flops a flush draw or straight draw. I really wanted to get these apps. But when I went to download them, I learned that you need a Windows OS, and I have a Mac. Damn! I was pretty bummed. Oh well.

I proceeded to dabble around in poker, progress a lot more slowly than I would have liked, and spend most of my time studying computer science. Life was fine.

A small project to dust off the rust

After about a year, I felt like it was time to move on. I was ready to freelance as a web developer. However, I had been doing computer-science-y things for a year and my web dev skills got pretty rusty, so I wanted to work on a project first to dust off that rust.

My skillset had been very JavaScript-centric, but I always thought the culture around Ruby was so cool, so I wanted to pursue that. But what project should I build? Hmmm. Oh! I know! I could build my own miniature version of Flopzilla and Equilab! It actually doesn't seem that hard! Seems like something I could do. And it seems like it'd be a lot of fun. Plus, I could use it to study poker. Awesome!

And so, that's what I pursue.

I work on it. I'm having a great time. Getting sucked in a little bit. I think it took about two months or so to have a decent version one. I wasn't really planning on spending that long on the project, but oh well, it's fine. I was really enjoying Ruby. So much nicer than JavaScript. I love how readable the code is.

Then... the planning fallacy happens. Over, and over, and over, and over, and over, and over, and over again. I think that pretty much sums up my next two years. In some sense at least.

Really getting sucked in

I think to myself, huh, this is pretty cool. I actually built a miniature version of these popular apps. I wonder if this could be a thing. I get pretty excited. I know a guy (well, really an acquaintance of an acquaintance) who played poker professionally. I get a hold of him and ask if he thinks this app I'm building could be a thing. He says that Flopzilla and Equilab are definitely better, but that if this is free, well, idk, maybe it could be a thing.

Good enough for me! Woooooooo hoooooooooooo!!! Let's goooooooooooooo!!!

Says my Monkey Brain.

Rational Self? He says:

Meh, idk if this is a good opportunity or not, but there's a couple more features I want to build that shouldn't take too long. Idk, maybe a month or two. Let's just give it a go. I'm getting good experience, after all. And I feel like this could get some traction with a) Mac users and b) people who want something for free, at the very least. So yeah, let's just bang out these next couple of features and proceed from there.

C'mon Rational Self. Will you ever stop falling for the planning fallacy?

So yeah, at that point, I basically just get sucked in. I keep thinking, "only another month or two". But things always end up taking longer.

At some point I deploy it so that it's live. When I test out the live version by running a simulation, I realize something: it's slow. Huh? Why is that? The development version has always been super fast. Why the discrepancy? Oh, I know: network latency! You see, I've been using my new friend Ruby on Rails. Which runs on the server. So when you click "Simulate", a request has to go out, over the internet, hit the server, run the simulations, then you have to wait for it to come all the way back to your laptop so that you can see the results. That back-and-forth from your laptop to the server takes time, and that time is why the live version appeared slow.

Fuck. That's just totally not acceptable, from a user experience perspective. As if there are actually other users out there having experiences. So what do I do? I just have to rewrite the whole thing to run on the client side. Remember how this was just supposed to be a little project to dust off my web dev rust?

I further justify the decision to rewrite it, because it'd be an opportunity for me to learn React. Previously I was an Angular guy, but in my year away from web dev React and Vue and these one way data flow frameworks became a thing. Data binding is bad now, apparently. So like, my skillset is pretty outdated if I don't know these new frameworks, right? I should take the time to learn them, right? Learning is Good, right? And besides, it won't take that long to rewrite it. The actual logic is all there in Ruby already.

So, that's what I do. I rewrite the whole thing in React. I forget exactly how long it took, but it took some time.

Guess what happens next? I decide to rewrite the whole thing in Vue! I actually remember how this went down in pretty good detail. There was a point where I wanted to do the equivalent of ng-repeat in React. I looked around, and couldn't find out how to do it. What?! That's such a basic thing. Why isn't there an easy way to do it. The React Way to do it just seemed really ugly. I was annoyed.

Then I ended up taking a trip to New York to visit my family. There was a day where I was in the city for a doctors appointment. I was getting a bagel in the morning. I remember this. I sat down to eat my bagel. I opened my phone and was browsing Hacker News. I came across a post comparing VueJS to the other frameworks. I sat there and read the post as I ate my bagel.


Rational Self: Yeah, I mean I guess that's not a bad idea. Learning is Good, after all. I'm not in a rush. Seems like a good thing to do.

And so, I rewrite the whole thing in Vue. I have to say, I do like Vue a lot.

Let me point something out though. At this point, I've been working on this project for... I don't know, maybe 6 months or something? A lot longer than I had initially planned.

Is this a real business?

And as I work on it, slowly but surely the idea starts to marinate in my head that this could be better that Flopzilla and Equilab. That this could be a real business.

So yeah, I rebuild it in Vue. I'm loving Vue. I'm loving the app. I'm thinking that I might be able to build something better than Flopzilla and Equilab. (Let's just say "Flopzilla" moving forward instead of "Flopzilla and Equilab". Flopzilla is the more substantial of the two.)

My memory for this point in the journey is a little bit fuzzy. I remember there being a good deal of time where I was in this no mans land where I wasn't sure if I wanted to pursue this as a business, but I did want to build "just one more feature". I basically just kept caving in and doing "just one more feature", while slowly thinking more and more, "Ok, I sorta think I could outdo Flopzilla. I sorta think this could be a business."

At this time, I told myself that it's actually pretty low risk. Well, what I mean to say is that it's a pretty high-floor sort of pursuit. Like, I'm not sure if I could outdo Flopzilla, but I'm pretty sure I could get somewhere in the ballpark. Yeah, I felt pretty sure of that. And Flopzilla doesn't even work on Macs. And it costs $30. Mine does work on Macs, and I could make it free. So... worst case scenario I should be able to get a bunch of Mac users and people who want something for free. I know ads are tough. I'm not saying I could get rich off of a free app, but I should be able to get a lot of users, and it should do something for me. It should be a pretty high-floor sort of pursuit. It's hard to see it just totally being a flop if I make it available for free. And it'll only take another couple months. And who knows. Maybe it ends up being really awesome and I can charge for it and make good money!

So, I decide to pursue it. Well, I don't think "pursue" is the right word. For a long time, my thinking was, "I'm not sure if this is worth pursuing long term, but I do think it's worth spending the next few months building out a few more features, so let's just do that for now." Let me emphasize that. Even like a year into this project, it wasn't something that I actually.... in my mind... explicitly... decided to pursue long term. I just kept saying "another month or two, another month or two". And yet it had been like a year. I spent a year doing something I never actually decided to do, in some sense.

But after a full year, I didn't really have much to show for. That really started to get to me and make me anxious. "How did this happen? How did I end up spending a year on something without ever deciding to do so?"

To make it worse, it really conflicts with some part of my identity. I like to think of myself as "good at startups". I failed with my first startup, and I always thought to myself that next time around, I will be smart and rational and consider lots of ideas and really think it through. I'll come up with some awesome plan for something that is very likely to succeed. Or at least that has a super high EV.

But where am I now? That is totally not how things went down with this app I'm working on. There was no master plan at all. I just kept chugging along like some sort of semi-conscious monkey. "Just another month or two. Just another month or two." Can't I open my eyes and think a little bit further down the line? Isn't imagining the future one of the things that makes humans human?

I know, I know. Humans are flawed and biased, and tons of people make these sorts of mistakes, and have these issues. But I expect better from myself. I know I can do better. Tsuyoku Naritai! I'm better than this. This is not what I'm capable of.

Struggling and moving slowly

But, I decide to chug along. Again, my memory feels pretty blurry. I forget exactly what my thought process was. I think it was that:

If I could go back a year, maybe this isn't the most optimal thing to work on. But I have all of this code. And I have this roadmap of features that I really want to build. I think it's at least worth taking 6 months or so to see it through, given where I'm at and how close I am.

As you can probably tell, around this time I really start to struggle emotionally. I felt pressure to succeed and make all this time I spent worthwhile. At least worth something in the end. I want to have something to show for.

I have thoughts that I'm 26 years old and I've always imagined myself way further along than I am now.

And I have this little voice in my head saying:

Hey Adam... it's been over a year... you don't have any users. This like totally goes against the whole lean startup thing, y'know.

And then I say in response:

I know, I know! But I really question whether the lean startup applies to this particular scenario. I know you want to avoid wasting time building things that people don't actually want. That's like the biggest startup sin there is. I know. But like, what am I supposed to do?
My hypothesis is that once my app gets to the point where it's in the ballpark of Flopzilla or better, that people will want to use it. It takes time to get to that point. There isn't really a quick two week MVP I could build to test that hypothesis. I'm already trying to avoid building non-essential features, and focus on getting to that point as quickly as possible. So what am I supposed to do?
If I released this and found that I had no users and no one wants this, what would that tell me? Just that people don't like this version of the app enough. Sure, ok. But the real question is whether they'll like the Ballpark Flopzilla version enough, or the Better Than Flopzillla version enough. My hypothesis is that they will, and releasing it now wouldn't invalidate that hypothesis. And I can't think of a way to test those hypotheses quickly. I think I just need to build it and see what happens.

I'm going to resist the temptation to respond to this right now. Right now I just want to tell the story. The story as it actually happened. But I do want to say that there were a lot of voices swimming around in my head questioning what I was doing.

Oh, one more thing. Throughout this time I'm also studying poker a little bit and trying to get good at it. It's going a lot more slowly than I wanted it to. I felt like an imposter not just as an entrepreneur, but as a poker player too.

I moved up the stakes online pretty slowly, but I was moving up. There was a point where I was stuck at $0.05/$0.10, but I did get past it. One thing that really ate at me though is that over my lifetime, I was down money at live $1/2. Live $1/2 is supposed to be the fishiest, easiest game ever. People love to talk about how incredibly bad $1/2 players are. And I'm down money in that game. And I've spent over a year building a poker app. And I'm supposed to be a smart person. Definitely surfaces feelings of being an imposter. At least for my Monkey Brain. Rational Self knew that it was just over a small sample size and I was in fact a profitable player at live $1/2. But it was still tough, and frustrating.

Such is life with poker though! That's part of what makes it such a great game! Go read some stories of the downswings that people go through.

Anyway, another big question that I debated with myself is whether or not to really release it and advertise it to the public. It had been over a year of development and I had a working, solid product, so when you zoom out, it seems pretty obvious that you should be getting it in front of as many users as possible. But... I didn't do that.

Here's why. I thought to myself, what exactly is the advantage of doing that? My big hypothesis is that Ballpark Flopzilla will succeed. I'm not there yet. Definitely at least a few months away. Sure, it's still possible that I get some users now, but who cares? I'll still get them in a few months anyway. It's not like I'd be losing them if I wait a few months.

Also, people like to say that the benefit to having users is that you can learn from them. But like, do I really need to release to the public for that? Aren't there other means to that end? Can't I just do traditional UX user research? Yeah, I think I can. Or so my previous self thought.

And so that's what I did. I tried to find people to sit with and go through the app with. I offered to buy lunch for anyone willing to do this with me, and tried to spread the word via online forums. Once in a while I'd find someone to do this with me, but to my surprise, not many people did. Weird.

Ok, but what's the downside, to releasing now, you ask? Well, I was very neurotic about bugs. I imagine the following thing happening:

I release some sort of beta version; people use it, they like it; but then someone realizes that my numbers are wrong. "It should be 81%, not 68%." They trash me in the poker forums; word gets out; I develop a bad reputation, people need to trust that the numbers I give them are right, that's absolutely essential!

So yeah, I really don't want that scenario happening. The risk of it happening seemed larger to me than the upside of getting a few users a few months earlier than I otherwise would.

And I'd always be telling myself: I'm not in a rush. So what if things take a little bit longer.

Lol! My Monkey Brain would be screaming at me that it needs some sort of validation. But then my Rational Self would say:

No, no, that's just an irrational feeling that I'm struggling to mitigate. We know it's silliness. Let's just ignore it.


Eventually, I did some tiny releases. And my Monkey Brain got some of that validation that it so desperately craved.

The big thing was posting to Reddit. I also posted to this popular poker forum called TwoPlusTwo, but I didn't get any responses there. But on Reddit, a lot of people told me the app was awesome, better than Flopzilla, etc, and thanked me for building it. I'd get a couple random emails from people telling this to me and thanking me. Man did this feel good. I really, really needed it.

Here's another high point. Maybe the biggest high point in my whole journey. This one I remember exactly where I was and how it went down.

My girlfriend had some friends over, and she likes to play loud music and have fun. Y'know, like normal people. I don't like that kind of stuff though. So I walked over to this awesome little hole in the wall place called Apache Taco Shop, hung out there, had a churro, and played some online poker.

I get bored when I play and pulled up YouTube to watch some poker videos in parallel to my playing. I know I shouldn't multitask like this, but I do it anyway. One of the videos was by a guy named Daniel Negreanu. He might be the most well known poker player in the world. People used to talk about him being one of the best in the world. Nowadays there's a cohort of younger more math-y people who are said to be better than Negreanu and his generation of players. But like, Negreanu is still fucking good.

I had like four tables open, I think. I have five windows on my screen. The left third is a YouTube video I have running. The right two thirds has four tables in a grid. Hands are popping in and out. Decisions to be made. My attention would drift to the YouTube video during the down moments in poker.

But as I had this video open, something caught my eye. In poker there's this thing called a hand matrix. It looks like this:

Normally in these sorts of videos the hand matrix comes from Flopzilla or Equilab. Sometimes it comes from some other random app. But this hand matrix was different.

It sorta looks like it's from my app. Premium Poker Tools. Could it be???????? NO WAY! I have Google Analytics and only get like 100 visitors a month. I only did a few small releases to Reddit. There's no way Daniel Negreanu is using my app and putting it in his poker videos!

But he did! It was my app! No doubt about it.

I swear, I almost cried. I was so happy.

I called my girlfriend, told her, and ran home like a little baby.

I mean, this was big news (or so I thought at the time). He's one of the best players in the world. And a huge name. So, if he's using my app, I think I have to assume that it's good! If anyone has good taste it should be him. This is pretty strong evidence! Think about it. Imagine a world where Daniel Negreanu likes my app, but everyone else doesn't. That really doesn't make sense. If anything, there's going to be some niche of people who really like it. So yeah, this made me feel very confident that I had something legitimate on my hands here. That I wasn't crazy.

And the thing is, there's still so much room for improvement! I had so many ideas and features I wanted to pursue. If he likes it now, just wait until I make it even better! This has got to have a really high ceiling!

So, at this point, I'm all in with the app. I've finally decided that it's what I'm going to pursue long(ish) term. I forget exactly when my mind really was on board with that idea. I think it happened before the Negreanu thing, but by the time the Negreanu thing happened, my mind was definitely on board.

Finally starting to charge

At some point, I decide to finally start charging for the app, and start trying to actually get users. Until now, I just posted to Reddit a few times with updates, and the app was free.

There was one Reddit post in particular that inspired me to move forward. People were saying that it's kinda crazy that my app is available for free and isn't more popular. A few said that it's something that they would pay for. One person (in an earlier post actually) even asked how he could donate money. I replied with my PayPal info. Then a different person donated $10. (A little weird that the original person didn't, but whatever.)

That $10 I received, it was the first money I had made as an entrepreneur, and that's after three years of working on things (two on my first startup, and about one on this one). It felt good. But weirdly enough, it didn't feel as good as I thought it should feel, if that makes sense. And that thought made me feel a little weird, a little guilty.

Whatever though. Overall, I was pretty happy. Things were looking pretty good. People were saying that they love my app and would pay for it. And that's with the app at its current point. In six, twelve, eighteen months, it should be way better. And the competition seems like they aren't actively developing things anymore. So it seems like I should be able to outdo them and get a pretty big piece of the pie.

So, I proceed to finish up a few features, and then get to working on building user accounts and credit card processing stuff. Seems like something that is very standard, and should be a piece of cake for a good web developer, which I like to think of myself as. But it ended up being a big rabbit hole for me. I could have built a working version in a week or so maybe, but I wanted to do it right. I wanted to get security right, UX right, and just in general make sure I'm following most of the best practices. I never know how to explain why code takes longer than it "should", but I think this process ended up taking me at least a month, maybe longer. The fact that it took so long made me feel a little bit of imposter syndrome. Although when I came across Authentication Still Sucks, it mitigated a lot of that feeling actually. At the end of the day, I was pretty happy with the final result.

Then there were some other rabbit holes I fell in to. Mostly consisting of business stuff. How do I want to monetize? Charging seems like it makes the most sense, but I should at least educate myself on what the other options are, and explore them a bit. I do that and decide to go with charging. But then there are a million other questions. Do I go monthly? Annually? Something else? Multiple options? Multiple tiers? $X.99 or $X.00? Stuff like that. I ended up spending some time doing research (hat tip to Price Intelligently), talking to people, and trying to make good decisions about all of this stuff. Maybe a week or so? I forget. I ended up deciding to charge $5.00/month.

Another small rabbit hole was looking at my options for credit card processing. I ended up going with Stripe, but I wanted to take some time to look at what the other options are, and what their costs and benefits are.

Eventually, I finish all of the grunt work of setting up the code for charging people. It happened at a good time for me. I finished about a day before I had a two week trip to visit some college friends and go to one of their weddings. It was a good stopping point for me code-wise, and a good time for me to take a little break.

Optimism and pessimism

After coming back from my trip and letting the dust settle a little bit, I found that some things went really well, and some things went really poorly.

I'll start with what went poorly: I wasn't getting any paid users. That was the big thing.

This guy from Reddit was my first user. I Skyped with him twice. He's a programmer + entrepreneur too, so we had some nice chats. He emailed me saying that he wants to subscribe as a paid user to support me, but also wanted to be upfront that he wouldn't have signed up if he didn't know me. But that's because he doesn't play poker enough. He does think the app is better than the competition.

Wonderful. Not exactly what I was looking for, but I'll take it!

My second user is a guy that I used to study poker with via Skype every week. But then one day, he just stopped responding to me. I'd reach out every couple months, but he just wouldn't respond to me. Really weird. But yeah, he subscribed as a paid user.

Third guy is someone random. Fourth guy is an IRL friend who I offered it to for free, but insisted on paying.

So, all of that was nice, but it doesn't exactly scream product-market fit.

Then there's the sign-ups. I offered a 14-day free trial. I was getting about one sign-up per day. It's something, but again, not really screaming product-market fit.

So yeah, that was the bad news. Now for the good news.

The good news is that a) I'd been getting good feedback on the app; people say it's really good, and b) I had a lot of affiliate leads. Let me explain what I mean by that.

When I first started charging, I considered doing affiliate marketing, where I give someone a link, and anyone who signs up via that link, they get some cut of the revenue, eg. 25-50%. So like if John Doe signs up with their link, and I'm giving them 50% revenue share, since I'm charging $5.00/month, I would give them $2.50/month for every month John Doe remains a user.

I initially decided to not do the affiliate stuff. I figured, why give up that 25-50% unnecessarily. Maybe the app takes off via word of mouth. I didn't actually expect that to happen, but I figured it was worth taking a stab. But after a month or so it became pretty clear that that wasn't going to happen, so I started to pursue affiliates.

I was doing pretty good! I got in touch with a bunch of people who said that they're interested. Many of them were authors of books that I've read. That was really cool to me. Until that point, I thought of book authors as some sort of celebrity. Writing a book seemed like a big deal to me. And they were books that were relatively popular too. Now I don't feel that same awe for people who have written books.

Anyway though, that's the part that was going well. I wasn't getting paid users organically. I wasn't even getting non-paid users organically (throughout the time the app was free, I'd only be getting like 200 users/month). But I was realizing how untrue "build it and they'll come" is, so it didn't worry me too much. In my mind, I had product validation. Enough people told me that the quality was really high. And my app's quality is only getting better, whereas the competition seemed stagnant. On top of that, I had all of these people saying that they were interested in working with me as an affiliate. People who were somebodies. Not really A-listers, but a solid mix of B-listers and C-listers. They seemed interested in working with me, and I felt pretty confident that once they start putting my app in their YouTube videos and blog posts, things would really ramp up for me.

More optimism, more pessimism

As time went on, the trends of the above section basically continued, but were amplified, I would say.

Time went on and I still had those same four users. And I'd still be getting about one sign up/day. Actually, less. So that's the "more pessimism" part. Pretty bad that I'm not growing or getting any traction.

The optimism part was that I had more people tell me they're interested in working with me as an affiliate. One was a legit A-lister. Let's talk about what happened with that.

Red Chip

I'm just going to go ahead and use real names. Screw it.

During the World Series of Poker, I tried to get out there and meet people. I posted on a site called Red Chip Poker that I'd love to meet up and hang out with anyone who's in town. No one responded, but one person invited me to a private poker game that they're having. So I went.

The game was super fun. By far the most challenging poker game I'd ever played in.

I ended up having lunch with someone from the game. Partly just chatting, and partly looking for advice on my app. He was staying with a guy named Doug Hull, who's a cofounder at Red Chip, a pretty well known poker site that does videos, blog posts, forum, podcast, all of that stuff. He said I should get on their podcast.

My first reaction was that Red Chip is an A-lister, and I wasn't ready to deal with A-listers. That was in my future plans, but I felt like I was too small to make my play at them. But, y'know what? Screw it. An opportunity is in front of me. Let's do it. I told him yes, and went with it. He introduced me to Doug, and a few weeks later Doug invited me over to his house to chat.

We chatted for like three hours. It was really nice for a lot of different reasons. One is just that there are only a handful of people in the world who build poker software, and he is one of them. So he understood things that no one else does, and it was nice to be understood in that sense.

I felt a little awkward about the fact that Doug has a product that is sort of a competitor to mine. But he seemed to not feel that way at all. I spent some time walking him through my app. We had a really great conversation. He gave me a ton of useful feedback and advice, and I explained the thought process behind a lot of my decisions. It didn't feel adversarial at all.

But it wasn't just feedback and advice. He wanted to work together.

An A-lister! Wants to work with me! I guess now is the right time after all.

What I was most interested in is something where they get me users for Premium Poker Tools. We talked about them putting a link on their site, promoting it, and getting some sort of revenue share.

He was also interested in that, but was more interested in me building other tools for Red Chip. He does his programming in MatLab, and doesn't know any web stuff. So he can build stuff, but isn't great with UI, and isn't able to publish it to the web. On the other hand, I do have those skills. So he was really excited. He had a lot of ideas that he wanted to work together on. It felt like he "found his guy". We didn't get into the details too much, but it seemed like he wanted to co-own anything we built.

I thought a lot about how I want to proceed after this. I was a little star-struck to be honest, because they are A-listers in the poker world in my mind. But at the same time, I wasn't really feeling a lot of Doug's plans to co-own stuff.

1) I really prefer to work alone. I like the autonomy. I want to be able to make decisions as I see fit, and not have to justify it to someone else. In particular, I didn't want to justify myself to Doug. I respect his thoughts, but I think there are a lot of times when he doesn't see things the same way that I do. Here's an example. I have a regular 2d graph on my app. Y'know, with x-y coordinates. When I showed it to him, he got excited and said that I should make it 3d or 4d, and how in his books he "one upped" me and has these 3d graphs. I seriously question whether users would be able to interpret those graphs and get value out of them, but Doug seemed to think it's just no big deal. Doug studied math in college and worked for Wolfram for a while, and seemed to not really understand how other people think.

2) I also felt like I didn't need him/them. All of the things he proposed are things that have been on my backlog. They're things I know how to build. I think the value he'd be providing would be product guidance, and marketing/exposure. I don't think I need the product guidance. And as for exposure, I could get that with other affiliates. I had a lot of people saying they were interested in working with me as an affiliate, so that seemed like something I could do.

But despite these things, when you zoom out, it seems a little stupid for me to turn down an opportunity to work with them, given that they're A-listers and I'm sitting here with no traction after almost two years. But that's what I decided I wanted to do. Because I trusted my zoomed in logic.

A couple days later, I had a Skype call with him and his partner James. It lasted a little bit over an hour. For the first half, I demoed the tools. James did most of the talking on this call, as opposed to Doug. He said he liked it! And he also had a bunch of useful feedback. The second half of the call, we talked more about business stuff and how to proceed. James was also interested in me building tools for Red Chip. He asked me how I felt about that. He threw out the idea of co-owning them. He also asked me how I felt about them sort of buying me out. Something along the lines of fixed price for PPT, and royalties + salary for future stuff. It was all very hand-wavy, but that was the gist.

I said no. I said I wanted to own anything I do and really pursue PPT. I told him how I had these huge visions (which I exaggerated a little bit to be sales-y). That I thought it could make many, many millions of dollars. Eg. maybe 100,000 users, and a $200 average LTV. He sort of laughed at that. Not in a mean way at all, but he just said that doesn't seem very likely, and that the poker market just isn't that big at all. That 1,000 users and a $50 average LTV is a lot more plausible.

I did update on this information, but not too much. It sounded like he was basing a lot of that on his numbers at Red Chip. But I saw the market for my app as way bigger. Just because they only have maybe 5k users doesn't mean that I am limited to that. In my mind, everyone needs software like mine to study with, whereas you don't really need to pay to be part of a training site. Reading books and consuming free content online like YouTube videos and blog posts will take you a long way. Yeah. IMO, those training sites really aren't necessary at all, given how much content is available for free/cheap. Also, I saw myself as capable of really skyrocketing past the competition and being the market leader, whereas there are a lot of poker training sites out there of similar quality to Red Chip. Which is to say there's a bigger market out there for me than for them. I didn't want to press him on this though. It didn't seem like it'd lead the conversation in a good direction.

We finished up by talking about putting my app on Red Chip and doing the revenue share thing. He said they're interested in that. He said it'd be nice if I could have Red Chip users get some sort of Red Chip-specific branding on the site. I don't love that idea, but I said sure. He ended by asking if I'm open to having a different price. He said he thought $5/month is way too low and that you can't have a real business with that price. I said I'm totally totally open to that, and that I am sort of winging it with price and I really respect their industry knowledge and yeah, that we can definitely talk more about that. So that's how we left it off, and we said we'd talk again in a week or two.

I delayed a little bit though. For two reasons. 1) After getting feedback from Doug and James, there was so much I wanted to improve with the app before really putting it out there. 2) I wanted to figure out what a good revenue share amount would be. 25%? 50%? I needed time for a) reading and talking to people for advice, and b) to see if my other affiliate leads would materialize (starting to get concerned that they haven't yet), so that I have leverage (BATNA) going into the conversation. 3) Another interesting opportunity popped up for me. I'll talk about that in the next section.

Short deck

I co-organize the Indie Hackers Las Vegas meetup. One of the guys at the meetup made an introduction for me to a guy named Brad. Brad is a former poker pro who is working on some poker security and crypto things now. We had lunch. It was... interesting.

For one, he said that he really doesn't like the market for the sort of app I'm building. He said the market is pretty small. Same thing James said. He said that yes, there are millions of people who play poker, but that no one actually studies. Everyone likes to say that they study and sound smart and cool, but very few people actually do. And that poker players are cheap and don't want to fork over money. And that the type of app I have is outdated. Nowadays it's all about something called Game Theory Optimal plays, which basically is figuring out how you'd play against a perfect opponent, such that you can't get exploited.

But I only updated my beliefs slightly from this conversation. I have to update somewhat, but the things he was saying just seemed wrong. Sure, there are a lot of people who are lazy and don't study, and there are people who don't want to fork over the money. But there are also people who do study and who are happy to fork over the money. The pie is really big with millions of players in the world, and I only need a slice of it.

I told him about my estimates. The poker subreddit has over 100k subscribers. A lot of educational YouTube videos get 100k+ views. A lot of the smaller channels get tens of thousands of views. All of these people are serious enough about poker where they are spending their free time trying to learn the game. To me, that is a potential customer. If you're spending your free time trying to learn the game, you should be in the market for poker software. All of the books and articles I read say that you need to have poker software like mine. Flopzilla is a household name. Everyone knows about it.

And as for poker players not being willing to spend money, that didn't seem true. Poker players often are people with money. There are a lot of wealthy recreational players. There's a lot of older ones who are retired and have some money. Younger players are often in tech fields, or playing poker professionally. And poker is all about ROI. And apps like mine easily pay for themselves. So I would think that poker players wouldn't hesitate to invest in something with a positive ROI. I mean, not everyone, but again, the pie is big, so even if a minority do, that's still awesome.

And the idea that poker is all GTO now is an idea I'm pretty familiar with. Some people think this way. They're wrong. But more to the point, it's definitely not the case that everyone thinks this way. Especially small-to-medium stakes players. Most of them don't think that way.

So, for all of those reasons, I didn't update too hard off of his skepticism.

Anyway, that wasn't really what he was there to talk about. He wanted something from me.

There's a version of Texas Hold'em (what people usually mean when they say "poker") called Short Deck Texas Hold'em. Basically, you remove the cards 5, 4, 3 and 2 from the deck, and now flushes beat full houses. Brad plays high stakes short deck professionally. He says that everyone is good at regular poker (long deck), but people are still learning short deck, so there are (more) fish to make money from.

More to the point, there isn't any publicly available software for short deck. He said he's positive that some of the super high stakes guys hire people privately to build them software, but there isn't anything available to the general public. So he wants me to adapt my app to make it work for short deck. He said that he would pay for it, and he knows a bunch of other people that would.

Furthermore, he was saying that he thinks it could be a great business opportunity for me. He said that there still aren't a lot of people who play short deck, so going mass market doesn't seem like it'd be the way to go, but the people who do play play super high stakes, and could be willing to pay a lot of money for the app. Like, hundreds of dollars a month. And possibly even thousands if I offer some sort of exclusive access, because these people really don't want their competitors getting access to it. He said that he is very, very well connected in the short deck poker world, knows everyone, etc. So we talked about how if I went through with this, we could do a thing where I give him a cut, maybe 25% or so, for anyone he gets to sign up.

I was hesitant to go off in a new direction, especially with the Red Chip thing being in the works, and having a bunch of other affiliates who said they'd work with me. But this did seem like a good opportunity. So I told him that I wanted to go home and see how long I think it'll take to build a short deck version, and as long as it's nothing too crazy, I'm in. Surely enough, it didn't seem like too much work to adapt it for short deck, so I texted him and said I was in.

Things fall apart

At this point, I end up taking a week or two to finish up something I was working on, and then I got started working on the short deck stuff. That took 2-3 weeks I think.

About a week after talking to the Red Chip guys, I texted Doug and asked if we could wait another week. He said sure. Another week passes, and I text him. He doesn't respond. Whatever. I need a little bit of time anyway. I want to finish up this short deck stuff, and more importantly, I want to see if other affiliates materialize to give me more leverage against Red Chip, and I want to talk to some more friends for advice on the revenue share amount I should do. Initially I was thinking 50%. Some said that's way too high, and 20-25% is better. Some said that's too low, and 50% makes sense when you're getting off the ground. A lot of mixed messages, so I don't really know what I should do.

Moving back to short deck, over the 2-3 weeks I work on it, I'm in touch with Brad via text. He's responsive and nice. Going well. A few days in he texts me and says his partner is going to give me $500 when I finish, as an incentive for me. Great!

Eventually I finish the short deck stuff. I have a call with Brad and his two business partners. First I demo it to them. They all love it.

We ended up spending a lot of time on that call talking about my regular long deck app. One of his partners was pretty quiet; it was a different guy named Cy who did the talking along with Brad. Cy basically gave me the same spiel as Brad, about how much he hates the business. Whatever. More updating, but still nothing crazy, for the same reason as before.

Cy has some different ideas as for how to monetize the short deck stuff. He wants to create a site, eg. shortdeckstrategy.com or something. The idea is to write some articles, put my app on the site, get visitors, and put an affiliate link to a poker site like Poker Kings, and make money when people sign up for Poker Kings. Brad's agreeing with Cy. So like, a totally different direction from what Brad and I talked about initially. Initially we talked about not going mass market, and instead selling to all of these high stakes players that Brad is supposedly so buddy-buddy with. Throughout that call, my head was spinning a little bit. There was a lot of fast talking.

At the end of the call, we agreed that they would use the app for a little while, test it out and stuff, and we'd all mull things over regarding how to monetize.

Then there's the question of how much they would pay me for the app. When Brad and I initially met, we threw around numbers like $50/month or $100/month. Nothing definite, just throwing numbers around. During this call when the topic came up, I just left the question to them and said "whatever you think is fair". Brad and Cy sort of looked at each other - to the extent that you can do that in a video call. Cy was hoping for $50/month. But Brad spoke up confidently and said let's do $100/month. Cy agreed, slightly reluctantly. And that was that.

Oh, Brad also said that he knows so many people in the poker world and can introduce me to some people who could maybe be affiliates for me for my regular PPT app (as opposed to the short deck one). One in particular - Ryan Laplante. We left it off saying he would get me in touch with Ryan and hopefully some others.

A few days go by. I haven't received any payment from them. I'm sure I'll get it though. I don't want to be pushy if we're going to be business partners.

I get my $100/month from each of them. But I don't get the $500.

Another few days go by, and I ask Brad about it. He's sort of my point-man.

I won't narrate the exact text history, but it was really weird. I also followed up on the intro to Ryan Laplante and others. And I asked him for Google ad advice, because he said he's good at that. A few other things I think. Sometimes he'd just straight up ignore me. Sometimes I'd get a short and cryptic response. For the $500, sometimes he'd ignore it, sometimes he said he'd ask Cy and then not get back to me.

I start to get annoyed at this. I don't want to work with someone who isn't responsive. And I definitely don't want to work with someone who promises me money and then doesn't give it to me.

Well, actually I'm not sure about this. I debate it internally with myself. Maybe I should just suck it up and deal with it, because it'd be too much to pass up the larger opportunity.

Let's jump back to the Red Chip thread. Eventually Doug gets back to me (he hadn't responded to my last text). He apologizes. I say no worries, let's schedule a time to chat again. His response to this was really weird. He said sure, want to come over to my house, or meet at the bar. I'm confused. James, his partner, the one who seems to be more in charge of business stuff, lives in Tennessee, and we're in Vegas. I say I want to talk about money and our next steps, and I think James should be there for that. His response to this really surprised and frustrated me. It was that James is a "hard guy to reach".

What?! This is your business partner. And we're in the process of working together. What's going on? It was as if our previous two conversations — the ones we spent 4+ hours on — didn't happen.

Eventually he says that if it involves money it needs to be in writing anyway, so why don't I write up my proposal and email it to them, and then we can talk afterwards. I don't love that idea, because to me this is a fluid conversation that involves back-and-forth. But sure. I email them.

I decide to totally err on the side of being generous. I was considering offering 25%, but I decide to go with 50% revenue share. So I say that in my email. I also say that I want to go with $5/month for now, the idea being that I don't think I could reach the masses — eg. 100,000 users — at a higher price. I said that I want to at least give that a shot. And if that doesn't work, then it means my users will be more niche and more serious players, in which case I agree with them that it makes sense to charge more.

Doug responds in this formal tone and says that they don't want to work with me.

What?!!!!! What on earth just happened. We had everything set up. I thought we were just negotiating the revenue share amount, and figuring out the next steps moving forward. I'm so confused!

He mentions very briefly that they don't want to work with me at the low revenue per user.

That just makes no sense to me. 1) Aggregate is what matters, not per user. There aren't really any marginal costs per user. Customer support would be the big one, but I'd be handling that, not them. 2) I was clear that I'd only want to pursue the low price if it gets tons of users. Revenue is what matters. 3) At the end of the day, I am flexible. It'd be nice if we could at least have a conversation about it, given that we had already spent 4+ hours talking with each other and were so close to working together.

So I respond and ask if he would mind explaining his thinking. He says they don't like the low price per user, because of the "fixed costs of partnership". That makes no sense to me. I didn't think the plan was to do any fancy lawyer stuff. And all I'd be looking for from them is to put the link on their site, and hopefully include it in their videos and blog posts as they see fit. So I don't know what just happened here. I would expect to at least have a conversation about it.

His response was very short and formal, again, and he clearly wasn't interested in talking more with me, so I gave up. But I had two small parting requests. The initial thing we talked about was me being on their podcast, so I asked if I could do that. He lied to me and said they only do the podcast "sporadically" now. It used to be once a week, now it's once every two weeks. The second thing was asking if they could include PPT in their Best Poker Software article, where they list out all of the options people have in terms of poker software. He said they only revisit that article once a year.

That was a total disaster. Let's get back to the short deck thing.

Actually, before that, I want to note that none of my affiliate stuff has materialized. All of the people who said that they're interested in working with me just haven't been responsive at all. I spent time trying to find other people to work with me. Vlogers, Twitch streamers, coaches, whoever I could find. I sent out a bunch of emails and messages, but nothing really materialized from that. Two leads. More on that later.

Also, I haven't gotten any new paid users. And sign ups has slowed to a crawl.

Around this time I tried to learn about marketing and stuff. Trying to figure out what else I could be doing to acquire users. I spent a lot of time on the code, and wanted to put on my marketing hat. I went through Julian Shapiro's Growth Guide, which I loved. I appeared on two podcasts, but they were both small, and didn't seem to drive any traffic, let alone sign ups or paid users. I set up paid ads on Google, Bing, Reddit, and TwoPlusTwo (a popular poker site). They didn't get me any paid users though.

Also around this time, I have lunch with a guy in the industry who knows his stuff. He tells me that he'd estimate Flopzilla to have between 1k and 10k purchases, at $25-35/user, which would mean a maximum of $350k. That is incredibly significant information. It should have blew me out of my chair, but what actually happened is that I started off thinking, "Meh. Maybe it's true, maybe it's not. Whatever." From there, I slowly moved away from that and towards, "Yeah, it's very true, and that means that I don't really have a business opportunity anymore."

Anyway, everything is totally falling apart for me right now. Let's get back to the short deck thing.

At some point I think through what they were saying on the call. At the time my head was spinning, but once the dust settled, going the mass market + affiliate link route did seem like a good way to monetize. So I write up an email to them explaining that I agree with that approach and what my thought process was. I ended by asking them what they think, and if we could set up a time to talk again. A week or two passes, and no one responds to that email.

I start getting a really bad vibe from the short deck guys. I start pushing for the $500 some more, and still don't get it. So I start thinking about it, and I decide that I don't think I should work with them. a) Our relationship has soured given how they've been treating me, and b) I really question whether I even need them. Their idea was to have that shortdeckstrategy.com site, make money with affiliate links, and put my app on there for free to drive traffic (I would upsell some tools) along with them writing a few articles. But I feel like the free software is the big driver of traffic, not the articles they would write, so why don't I just put the short deck thing out there for free and put my own affiliate link on it? Why do I need them? The reason would be if they are so well connected and amazing that they figure out how to drive a bunch of traffic to the site. Something I clearly struggle to be able to do. But if they're so well connected, why are they the only three signed up for the short deck app right now? And why hasn't Brad been able to introduce me to anyone, like he said he would? It just felt fishy. Plus, the benefit would need to be quite large for me to justify working with people I don't like, and the benefit did not seem that large at all.

So I finally manage to get a lunch scheduled with Brad. Previously we had scheduled times to talk, but he flaked on me, twice I think. Before this lunch I really pushed for the $500. He finally responded and said that Cy thought he would be getting the app for $50/month, not $100/month, and that's why he hasn't paid me the $500. Ugh! That's just wrong on so many levels. I respond to Brad saying that I think that's wrong and that I am expecting to receive that money.

I decide going into it that I'm basically done with them, and only would possibly work with Brad if a) I get my $500 (I'm really bitter about that if you can't tell), and b) he wants to go the route of getting people to sign up for the short deck app in exchange for 25% revenue share, not their shortdeckstrategy.com thing.

So, we have lunch. I get to the restaurant. And I see Cy sitting there early before Brad gets there. I actually didn't even recognize him at first, what was awkward, but eventually I sit down and say hi. He immediately gives me the $500. Cool. Got that over with. That was actually the big thing I wanted to accomplish by having lunch with... well, I didn't know Cy was going to be there actually, but I was going to talk to Brad about it. But yeah, happy I got my money. No apology from either of them though, which isn't good.

During the lunch Cy vents a little more about how he doesn't think my long deck app will succeed. Why are we talking about this again? It has nothing to do with them. Whatever. I'm sorta just passing time. At some point I plan on saying how I don't want to work with them on the shortdeckstrategy.com thing. I don't want to say it too early on though, because then what are we supposed to do for the rest of the lunch?

But eventually I get to it and tell them I don't see that it makes sense for us to work together on that, and that I would prefer to do it on my own. Brad is pretty taken aback. Looks like he didn't know how to respond. He says nicely that if I'm going to do it on my own, then I'd be competing with them, and it wouldn't make sense for us to work together. I say I agree. This is towards the end of the lunch, and I make a last attempt to see if Brad wants to do the thing where he gets 25% for anyone who he gets to sign up. He says no. Cy mentions that he's "ran out of energy". We leave, and that's that.

At the end of all this, I finally start questioning whether this is something I should continue to work on.

Things continue to fall apart

At this point there are three big affiliates who said they were interested in working with me that I have been hoping to work with.

The first is a guy who I was introduced to through a friend, and has a popular vlog. After the friend made the intro via text, we exchanged emails and he said he's interested and we'd set up a time to talk. Months had passed, and I had reached out via email maybe six or seven times to check in, and never got a response. Then one day I'm at the casino playing some poker, and I see him in person at the water cooler, so I walk over. He apologizes and says that he's just so busy and has so many of these offers, and that he doesn't even like promoting other products in the first place. I make a small push, saying that it's a great product and it'd be super low-effort for him: just put a link in the description. But he didn't seem interested, so I backed off.

The second is a guy who I really like and have been in touch with for about six months. He just keeps saying that he wants to work together but is too busy at the moment and needs to finish up a few things before we dive into it. I've given up on him at this point.

The third is one is really frustrating. I appeared on his podcast, and it went pretty well. After the podcast interview, I talked with him about working together as an affiliate. I offered 50% revenue share if he's going to be an active partner, or 25% if passive. For active, I just want him to produce maybe 2-3 blog posts or videos a month. For passive, he could just throw the link wherever and hope people click it. He said he's in for the active deal. Things were very clear, and it looked like we were ready to move forward. Then, well, he just disappears. A month and a half has passed and he hasn't responded to any of my follow up emails.

So at this point, it seems that I've really ran out of gas as far as partnering with affiliates goes.

I try some other things though. One thing I try is changing the pricing from $5/month to $25 as a one time fee for the basic plan, or $75 for the premium one. But that didn't do anything.

But as I am doing these new prices, I realize that there's a bug. A really, really, bad, bug. Perhaps the worst kind of bug possible. Can you guess what it is?

People who are signed in, when they try to go to the purchase page, it says they are unauthorized. Sure enough I see the typo in my router file. People who want to pay me haven't been able to pay me!

Then I learn that the little chat widget I have, people have been trying to use it to tell me that there's the bug for over a month! And I haven't responded to any of them! The widget is supposed to forward me an email of the messages I get, but I haven't been receiving those email notifications due to some weird incompatibility issue with my mail provider. So I just have been assuming this whole time that everything is fine.

What a nightmare. People try to pay me. Bug prevents them from paying. People try to let me know about the bug. They don't get a response.

Anyway, I also try to do the short deck thing on my own. I made one tool available for free and another for $150 as an upsell. I'm going to put an affiliate link on the free tool to see if I could make some money that way, but I haven't been getting any pageviews for it.

I spent some time working on a blog, and posted a few articles to poker forums, but that hasn't gotten me any traction either.

Throughout all of this, I'm moving closer and closer to calling it quits. I'll talk about that in the next post.


12 comments, sorted by Click to highlight new comments since: Today at 10:41 PM
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This is fantastic, and I imagine hard to write. Thank you for sharing.

Yes, very hard to write, but it makes it feel very worth it if people are enjoying it :)

This is a great authentic diary of a certain type of smart startup founder's experience. I'm sure there have been dozens of other founders who have similar stories and never wrote them up like this.

But I really question whether the lean startup applies to this particular scenario. I know you want to avoid wasting time building things that people don't actually want. That's like the biggest startup sin there is. I know. But like, what am I supposed to do?

Yep, that's the internal monologue of most founders. The siren song is "Surely I can't put this in front of users this week". You have to be Odysseus ignoring the sirens.

My hypothesis is that once my app gets to the point where it's in the ballpark of Flopzilla or better, that people will want to use it. It takes time to get to that point. There isn't really a quick two week MVP I could build to test that hypothesis. I'm already trying to avoid building non-essential features, and focus on getting to that point as quickly as possible. So what am I supposed to do?

The goal is to validate that specific people exist who have a need for what you're building. But the "specific people" part of that sentence is more important than the "what you're building" part. Identify them now and talk to them, then ask yourself what is the minimal thing you can do to get them engaged with your product/service.

When you scope a product for only one specific workflow of one specific person, it can be much leaner than what you otherwise would have built as an MVP.

Re needing to be better than Flopzilla: If a specific target user is currently using Flopzilla, how about a workflow where they keep Flopzilla open but also your product at the same time, and they pull up your product in a few narrow situations where it's differentiated from Flopzilla? It'll be a janky experience, and that's fine. It should be possible to get a few specific users using something janky like that as your initial validation.

This is a great authentic diary of a certain type of smart startup founder's experience. I'm sure there have been dozens of other founders who have similar stories and never wrote them up like this.

Thank you! Yeah, I tried to be as honest as possible telling the story. I think it makes it easier to learn lessons, more fun to read, and for some reason, easier to write.

The goal is to validate that specific people exist who have a need for what you're building. But the "specific people" part of that sentence is more important than the "what you're building" part.

That's a great point. In my mind at the time, the "specific people" part was already validated due to the fact that hundreds of thousands of people use Flopzilla and similar apps, or so I thought. But moving forward, I totally agree that it's something that I should have actually validated.

(FWIW I have a third post coming out soon where I reflect on the lessons I've learned. If you don't mind, I'd love to DM you when it's out, because I'd love to hear more of your thoughts.)

Sure feel free to DM.

In my mind at the time, the "specific people" part was already validated due to the fact that hundreds of thousands of people use Flopzilla and similar apps, or so I thought.

"Person who uses Flopzilla" isn't maximally specific, compared to knowing their name and talking to them :)

Yeah, I’m not sure how big the market is for a poker software. There aren’t that many people playing poker and a vast majority of them play it casually with no software. So even if you capture the entire market, it still might be only 1000 people or so.

As for people who say they are interested but then flake, Sebastian Marshall has the perfect word for them: jokers. Just ignore them immediately and move on. If someone wants to do business, you’ll feel it.

I did a web startup too for a few years. And everything took me longer than expected as well. Including authentication. It’s just a fact of life; but hopefully we can plan better now.

Thank you for your thoughts.

So even if you capture the entire market, it still might be only 1000 people or so.

Good to get another data point on this, thanks.

If someone wants to do business, you’ll feel it.

I suppose. But then again, there's the law of opposite advice thing. My thoughts are that there's something also to be said about perseverance.

I did a web startup too for a few years. And everything took me longer than expected as well. Including authentication. It’s just a fact of life; but hopefully we can plan better now.


(I promoted this to frontpage, though I usually leave posts like this on personal blog, because it does actually cover a bunch of general lessons and I think is actually of pretty broad interest)

All the deals falling through really felt familiar to my experience with my first startup. There was a week where we went from about $100,000 in handshake deals to $0. We shut down the next week.

One of the things I learned from that experience was that an effectuative strategy really only works if you have strong/solid relationships with your partners or deals in writing, not just acquaintances and handshake deals. Definitely taking that learning into the next startup.

Wow, that must have really sucked to lose out on $100k. I can't imagine what that's like, things never got that concrete for me.

I think you're probably right about acquaintances + handshake deals, but it's still a little counterintuitive to me. There's a lot of things that I think of as basic human decency, and expect 99% of the population to do. Following through on a handshake deal is one. Not ghosting people is another. It still feels tempting to me to continue with those expectations, but Rational Self feels pretty confident that the expectations are unrealistic.

Thanks for writing this. I've been considering trying a software startup at some point and I think your lessons from this will help me a lot. I've been considering doing something with RSS readers, since it's a tool I use and I have experience working with other people on them, but I definitely need to (1) do some market research to make sure it's even plausible that I could make money, (2) look into how to market it / whether I need a cofounder or if I could approach people who could help spread the word, and (3) if I do it, make sure I can come up with something fast that people could immediately use, since I was also leaning toward "do the same thing as the market leader but better", and I think you've convinced me that that's a scary place to go. I might plausibly be able to be better than the market leader _at one thing_ and then add more features though.

(I'm brendanlong on Slack by the way, so we've already talked about this but I still found the articles really interesting)

Thanks, it's awesome to hear that you found it helpful!

I'm always down to talk more about the RSS reader idea. But yeah, I think 1, 2 and 3 are very good ideas.

As for the "do the same thing as the market leader but better" thing, I also feel skeptical about it now. There was a large period of time where people were telling me that they liked my product more than Flopzilla, and I was offering it for free, and I wasn't getting users! I never would have expected that to happen.

That's not to say that "do the same thing as the market leader but better" is always a bad idea, but I think it needs to be coupled with "and I have some good ideas about how to do customer acquisition" not "and once I do, I expect that users will just come". For the latter, my thinking now is that you need to 10x your competitor or something, like the YC guys encourage you to do iirc.